Acetamide → 2-Acetamidoethyl acetate

Participants

Reaction Steps

Ten grams of sodium hydroxide was suspended in 50 ml of N,N-dimethylacetamide, followed by a further addition of 12 g of acetamide, 0.05 g of phenothiazine and 36 g of 2-chloroethyl acetate. A reaction was allowed to take place at 40° C. for 4 hours with stirring. After the completion of the reaction, the reaction solution was filtered to separate off all the undissolved materials. Under reduced pressures, N,N-dimethylacetoamide and unreacted 2-chloroethyl acetate were distilled off. After adding 100 ml of benzene and 50 ml of distilled water to the residue, the mixture was thoroughly agitated and separated into two layers. The aqueous solution layer was extracted twice with 50 ml of benzene. The benzene layers were combined and dried with magnesium sulfate. The thus-dried benzene layer was subjected to a distillation under reduced pressure. A fraction was collected at 138-140° C./ 2 mmHg, thereby obtaining 22 g of N-acetoxyethylacetamide (yield: 74%). The reaction system in the above reaction contained water of the order of 5000 ppm or so.

Provenance & Evidence